Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 57901661 | HCID 57901661 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57901758 | HCID 57901758 | 43% |
Reaction Steps
A mixture of ethyl 5-fluoro-1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.45 g), 60% sodium hydride (52 mg) and N,N-dimethylformamide (10 mL) was stirred at 4° C. for 30 min. Methyl iodide (0.095 mL) was added to the solution, and the mixture was stirred at room temperature for 2 days. The reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-2:8) to give the title compound (0.20 g, yield 43%) as colorless prism crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957070B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-4712b702876048e3a894b0b3e6c81ea0 |
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| Source note | uspto-grants-2015_02 |
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